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1 Supporting Information Postfunctionalization of periodic mesoporous silica SBA-1 with magnesium and iron(ii) silylamides Thomas Deschner, a,b Michael Klimpel, c Maxim Tafipolsky, c Wolfgang Scherer, d Karl W. Törnroos b and Reiner Anwander* a *a Institut für Anorganische Chemie, Eberhard Karls Universität Tübingen, Auf der Morgenstelle 18, Tübingen, Germany. Fax: ; Tel: ; Reiner.Anwander@uni-tuebingen.de b Kjemisk Institutt, Universitetet i Bergen, Allégaten 41, 5007 Bergen, Norway c Department of Chemistry, Technische Universität München, Lichtenbergstr. 4, D Garching bei München, Germany d Institut für Physik, Universität Augsburg, Universitätsstraße 1, D Augsburg, Germany 1
2 Synthesis Procedures Materials. SBA-1 1: C 18 TEABr (5.70 g, mmol), concentrated HCl (37 wt %, g, 3.18 mol), and distilled water (598.5 g, mol) were combined, and the resulting mixture was vigorously stirred until a homogeneous solution formed (ca. 30 minutes). The solution was cooled to 0 C in an ice bath and g (65.67 mmol) of TEOS was slowly added. Stirring was continued for 4 h at 0 C, and then the reaction mixture was heated in a polypropylene bottle to 100 C and maintained there for n hours without stirring (n =1; 6). The solid product was recovered by filtration (without washing) and dried at ambient temperature. The assynthesized material was calcined at 540 C (air, 5 h) and dehydrated in vacuo (270 C, 10-4 Torr, 8 h). The molar composition of the synthesis gel was 1:5:280:3500 C 18 TEABr:TEOS:HCl:H 2 O. Grafting Precursors. [Mg{N(SiHMe 2 ) 2 } 2 ] 2 (2). To a solution of 1.87 g HN(SiHMe 2 ) 2 (14.00 mmol) in 5 ml hexane a 1M Mg(n-Bu) 2 solution in heptane (7 ml, 7.00 mmol) was added slowly. The solution was stirred for 4 h at ambient temperature during which gas evolution was observed (n-butane). Afterwards, the solvent was removed in vaccuo. Two times subsequent crystallization in n-hexane at 35 C yielded 1.80 g (6.23 mmol, 89% yield) colourless crystals of the pure compound. Analysis calculated for C 8 H 28 N 2 Si 4 Mg (wt%): C, 33.25; H, 9.77; N, Found: C, 33.64; H, 9.04; N, DRIFT (KBr, KBr, cm -1 ): 2953s, 2897w, 2078s, 2047s, 1781w, 1428w, 1410w, 1259s, 1247s, 1058s, 957s, 889s, 843s, 793s, 775s, 765s, 737w, 709w, 692w, 683w, 634w, 619w, 488m, 408w. [Mg{N(SiMe 3 ) 2 } 2 ] 2 (3). To a solution of 2.26 g HN(SiMe 3 ) 2 (14.00 mmol) in 5 ml hexane a 1M Mg(n-Bu) 2 solution in heptane (7 ml, 7.00 mmol) was added slowly. The solution was 2
3 stirred for 4 hours at ambient temperature during which gas evolution was observed (nbutane). Afterwards, the solvent was removed in vaccuo. Two times subsequent crystallization in n-hexane at -35 C yielded 2.11 g (6.11 mmol, 87% yield) colourless crystals of the pure compound. Analysis calculated for C 12 H 36 N 2 Si 4 Mg (wt%): C, 41.77; H, 10.52; N, Found: C, 41.51; H, 11.14; N, DRIFT (KBr, KBr, cm -1 ): 2946s, 2897m, 1462w, 1450w, 1429w, 1391w, 1316w, 1296w, 1251m, 1239s, 1184w, 1025m, 986s, 876s, 841s, 826s, 780m, 747m, 712w, 664m, 621w, 610m, 435w. [Fe II {N(SiHMe 2 ) 2 } 2 ] 2 (5). A solution of 4.40 g LiN(SiHMe 2 ) 2 (31.56 mmol) in 5 ml THF was added slowly (highly exothermic reaction) to a milky solution of 2.04 g FeCl 2 (15.78 mmol) in 5 ml THF. The solution turned dark brown immediately. After one hour of stirring at ambient temperature, the solvent was removed. Centrifugation and three times washing of the remaining solid with n-hexane led to a dark green/black solution. The washing fractions were collected and n-hexane was removed. Extraction with n-hexane and two times subsequent crystallization in n-hexane at 35 C yielded 3.06 g (9.56 mmol, 61% yield) green crystals of the pure compound. Analysis calculated for C 8 H 28 N 2 Si 4 Fe (wt%): C, 29.98; H, 8.81; N, Found: C, 29.49; H, 9.01; N, DRIFT (KBr, KBr, cm -1 ): 2949s, 2899m,2116s, 2083s, 1418w, 1250s, 1001m, 889s, 839s, 804m, 788m, 773m, 727w, 628w, 604w 472w. Hybrid Materials. SiHMe (1a). Dehydrated SBA-1 (1) (100 mg) was suspended in 5 ml of n- hexane. Under stirring, 200 mg (1.50 mmol) of HN(SiHMe 2 ) 2 was added. The suspension was stirred for 18 h at ambient temperature and nonreacted silazane separated via combined n-hexane washings centrifugations (3 ). Subsequently removing the remaining solvent by drying under vacuum yielded the hybrid material (81 mg). Analysis found (wt%): C, 7.36; H, 1.90; N,
4 Si(vinyl)Me 2 ) 2 } 2 ] (1j). A suspension of 56 mg of the hybrid material 1i in 5 ml n-hexane was prepared. Under stirring, 200 mg (1.08 mmol) of HN[Si(vinyl)Me 2 ] 2 was added. After stirring the suspension overnight at ambient temperature, nonreacted silazane was separated via combined n-hexane washings centrifugations (3 ). Subsequently removing the remaining solvent by drying under vacuum yielded a slightly yellowish hybrid material (65 mg). Analysis found (wt%): C, 8.99; H, 2.08; N, 0.19; Mg, n.d.. Si(vinyl)Me (1k). A suspension of 96 mg of the SBA-1 material (1) in 5 ml n- hexane was prepared. Under stirring, 500 mg (2.70 mmol) of HN[Si(vinyl)Me 2 ] 2 was added. After stirring the suspension overnight at ambient temperature, nonreacted silazane was separated via combined n-hexane washings centrifugations (3 ). Subsequently removing the remaining solvent by drying under vacuum yielded a white hybrid material (80.7 mg). Analysis found (wt%): C, 12.65; H, 2.57; N,
5 Figure S1. PXRD of SBA-1 1. Figure S2. Nitrogen adsorption/desorption isotherms and corresponding BJH pore size distribution of SBA-1 (1) ( ), SiHMe (1a) ( ), [Mg{N(SiHMe 2 ) 2 } 2 ] (1b) ( ) after 18 h grafting and [Mg{N(SiHMe 2 ) 2 } 2 ] (1e) ( ) after 4d grafting. 5
6 Figure S3. BJH pore size distribution of SBA-1 (1) ( ), SiHMe (1a) ( ), [Mg{N(SiMe 3 ) 2 } 2 ] (1c) ( ) after 18 h grafting and [Mg{N(SiMe 3 ) 2 } 2 ] (1f) ( ) after 4 d grafting. Figure S4. BJH pore size distribution of SBA-1 (1) ( ), SiHMe (1a) ( ), Mg[N(SiPhMe 2 ) 2 ] (1d) ( ) after 18 h grafting and Mg[N(SiPhMe 2 ) 2 ] (1g) ( ) after 4 d grafting. 6
7 Figure S5. Nitrogen adsorption/desorption isotherms and corresponding BJH pore size distribution of SBA-1 (1) ( ), SiHMe (1a) ( ), [Mg{N(SiHMe 2 ) 2 } 2 ] (1b) ( ) after 18 h grafting and [Fe II {N(SiHMe 2 ) 2 } 2 ] 2 ) 2 } 2 ] (1h) ( ) after 4 d grafting. Figure S6. BJH pore size distribution of SBA-1 (1) ( ), SiHMe (1a) ( ), [Mg{N(SiHMe 2 ) 2 } 2 ] (1e) ( ) after 4 d grafting and [Fe II {N(SiHMe 2 ) 2 } 2 ] 2 ) 2 } 2 ] (1i) ( ) after 4 d grafting. 7
8 Figure S7. Nitrogen adsorption/desorption isotherms and corresponding BJH pore size distribution of SBA-1 (1) ( ), SiHMe (1a) ( ), Si(vinyl)Me 2 ) 2 } 2 ] (1j) ( ) and Si(vinyl)Me (1k) ( ). Figure S8. IR spectra (DRIFT) of mesoporous silica SBA-1 (1) and hybrid materials SiHMe (1a), [Mg{N(SiHMe 2 ) 2 } 2 ] (1b) and [Mg{N(SiHMe 2 ) 2 } 2 ] (1e) and precursor [Mg{N(SiHMe 2 ) 2 } 2 ] 2 (2) in the range of cm -1. 8
9 Figure S9. IR spectra (DRIFT) of mesoporous silica SBA-1 (1) and hybrid materials SiHMe (1a), [Mg{N(SiMe 3 ) 2 } 2 ] (1c) and [Mg{N(SiHMe 2 ) 2 } 2 ] (1f) and precursor [Mg{N(SiMe 3 ) 2 } 2 ] 2 (3) in the range of cm -1. Figure S10. IR spectra (DRIFT) of mesoporous silica SBA-1 (1) and hybrid materials SiHMe (1a), Mg[N(SiPhMe 2 ) 2 ] (1d) and Mg[N(SiPhMe 2 ) 2 ] (1g) and precursor Mg[N(SiPhMe 2 ) 2 ] 2 (4) in the range of cm -1. 9
10 Figure S11. IR spectra (DRIFT) of mesoporous silica SBA-1 (1) and hybrid materials [Mg{N(SiHMe 2 ) 2 } 2 ] (1b), [Fe II {N(SiHMe 2 ) 2 } 2 ] 2 ) 2 } 2 ] (1h), [Mg{N(SiHMe 2 ) 2 } 2 ] (1e) and [Fe II {N(SiHMe 2 ) 2 } 2 ] 2 ) 2 } 2 ] (1i) and precursor [Fe II {N(SiHMe 2 ) 2 } 2 ] 2 (5) in the range of cm
11 Figure S12. IR spectra (DRIFT) of the silazane HN[Si(vinyl)Me 2 ] 2 and the hybrid materials Si(vinyl)Me 2 ) 2 } 2 ] (1j), Si(vinyl)Me (1k). 11
12 Table S1. Analytical data of the vinyl-functionalized materials Sample/Precursor as[m 2 /g] a D me [nm] b V p [cm 3 /g] c C [wt%] d N [wt%] d 1 SBA-1 (a = 8.50 nm) a SiHMe j Si(vinyl)Me 2 ) 2 ] k Si(vinyl)Me a Specific BET surface area. b Pore diameter calculated according to Ravikovich and Neimark; 7 all samples were pretreated at 250 C (parent materials), 100 C (silylated samples) and 25 C (grafted samples) respectively in vacuo until the pressure was <10-3 Torr. c Pore volume determined at the relative pressure p/p 0 = d Elemental analysis obtained after treatment at 100 C in vacuo (<10-3 Torr). 12
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